# 5290 HILLSIDE Drive, Warrenton, VA 20187 > **TL;DR:** 5bd/5ba single family, $825,000 ($195/sqft), built 1979, 4,228 sqft. > Fireplace, A/C. Est. $4,413/mo. Listed 11 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $825,000 | | Price/sqft | $195 | | Bedrooms | 5 | | Bathrooms | 5 full | | Square Feet | 4,228 | | Year Built | 1979 | | Lot Size | 69,696 sqft (1.60 acres) | | Stories | 1 | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 11 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $4,172 | | Estimated Insurance | $241 | | **Total** | **$4,413** | ## Key Amenities - Fireplace - A/C ## Property Highlights - Built in 1979 - 1.60 acre lot - Fireplace ## Description ### Agent Description AMAZING VALUE! TWO COMPLETE LIVING SPACES - ONE PROPERTY. Rare multigenerational/income producing opportunity on the DC side of Warrenton! A beautifully updated main home PLUS an approximately 1,600-sq.-ft. private apartment with its own kitchen, bedroom, handicap accessible bathroom, entrance, HVAC, water heater and additional basement space. Welcome to this truly one-of-a-kind property offering the perfect blend of flexibility, privacy, and modern updates on 1.5 acres with a flat, usable backyard. With no HOA, you'll have the freedom to bring your chickens, start a garden, park your RV or boat, or simply enjoy the space without restrictive covenants. Whether you're looking for multigenerational living, an income-producing opportunity, or simply extra space for guests, this turnkey home delivers. The standout feature is the approximately 1,600-square-foot private apartment addition, fully remodeled in July 2026, with its own main-level entrance and welcoming front porch, this thoughtfully designed space features freshly refinished hardwood floors, soaring vaulted ceilings, fresh paint, a spacious bedroom overlooking the private backyard, and a beautifully renovated handicap-accessible bathroom. The updated kitchen (July 2026) includes a gas range, dishwasher, and modern finishes. The apartment also includes its own private basement with laundry, a remodeled full bathroom, and a separate exterior entrance. Previously configured with a kitchenette, the existing hookups make it easy to convert the space back into a kitchenette, creating an ideal studio apartment or potential sixth bedroom with its own private living area. A brand-new HVAC system and water heater provide added peace of mind. For maximum flexibility, the apartment also connects to the main home through secure double doors, allowing complete privacy for rental use while maintaining the option to seamlessly incorporate it into the main residence. The main home was extensively remodeled in 2016 and features an impressive gourmet kitchen with a gas cooktop, stainless steel appliances, upgraded cabinetry, and two beautiful 1800s English yellow pine antiques that were thoughtfully repurposed into a stunning 6-foot kitchen island and an undermount double-sink cabinet, all topped with durable, heat-resistant quartz countertops. Rich walnut hardwood flooring flows throughout the main level, where you'll also find a cozy gas fireplace, three spacious bedrooms, and two beautifully updated full bathrooms. The walkout lower level offers even more living space with a large recreation room, a fourth bedroom, and a remodeled full bathroom. Fresh paint and new carpet throughout the home make it completely move-in ready. Major system updates include the roof, windows, HVAC systems, hot water heaters, and deck-all replaced within the past 10 years, making this home as practical as it is beautiful. Step outside to enjoy the oversized deck overlooking a completely private, flat backyard-perfect for entertaining, gardening, or simply relaxing in your own peaceful retreat. Ideally located on the highly desirable DC side of Warrenton, just 1/2 mile from Route 29, this home offers exceptional convenience for commuters, with I-66 and the Gainesville commuter lot just 10 minutes away. Enjoy quick access to shopping and dining at Virginia Gateway, including Wegmans, Target, movie theatre, restaurants, breweries, wineries, golf courses, parks, and the charm of Historic Old Town Warrenton-all while coming home to the peace and privacy of country living. ## Location - **Address:** 5290 HILLSIDE Drive, Warrenton, VA 20187 - **County:** FAUQUIER - **Neighborhood:** BALDWIN RIDGE - **Coordinates:** 38.76288, -77.722 - **Google Maps:** https://www.google.com/maps?q=38.76288,-77.722 ## Listing Agent - **Name:** Vanessa Ann Gregg · **License:** 0225242420 - **Brokerage:** Pearson Smith Realty, LLC - **Broker Phone:** (571) 386-1080 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/5290-Hillside-Dr_Warrenton_VA_20187_M52545-14837?f=listhub&s=TRENDPA&m=VAFQ2024370&c=propsimple) ## Photos ![5290 HILLSIDE Drive - Photo 1](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f860611200r.jpg) ![5290 HILLSIDE Drive - Photo 2](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1949371680r.jpg) ![5290 HILLSIDE Drive - Photo 3](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2297074354r.jpg) ![5290 HILLSIDE Drive - Photo 4](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2083937616r.jpg) ![5290 HILLSIDE Drive - Photo 5](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1170384392r.jpg) ![5290 HILLSIDE Drive - Photo 6](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2028378027r.jpg) ![5290 HILLSIDE Drive - Photo 7](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f583654044r.jpg) ![5290 HILLSIDE Drive - Photo 8](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2915503616r.jpg) ![5290 HILLSIDE Drive - Photo 9](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2298867509r.jpg) ![5290 HILLSIDE Drive - Photo 10](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1169668646r.jpg) ![5290 HILLSIDE Drive - Photo 11](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1719807288r.jpg) ![5290 HILLSIDE Drive - Photo 12](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f898533222r.jpg) ![5290 HILLSIDE Drive - Photo 13](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3996869164r.jpg) ![5290 HILLSIDE Drive - Photo 14](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1209209538r.jpg) ![5290 HILLSIDE Drive - Photo 15](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f414316811r.jpg) ![5290 HILLSIDE Drive - Photo 16](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f812470125r.jpg) ![5290 HILLSIDE Drive - Photo 17](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1477493629r.jpg) ![5290 HILLSIDE Drive - Photo 18](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3722055259r.jpg) ![5290 HILLSIDE Drive - Photo 19](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f353489185r.jpg) ![5290 HILLSIDE Drive - Photo 20](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1180025425r.jpg) ![5290 HILLSIDE Drive - Photo 21](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f932382154r.jpg) ![5290 HILLSIDE Drive - Photo 22](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3905427513r.jpg) ![5290 HILLSIDE Drive - Photo 23](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2477705734r.jpg) ![5290 HILLSIDE Drive - Photo 24](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3268948078r.jpg) ![5290 HILLSIDE Drive - Photo 25](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1928063350r.jpg) ![5290 HILLSIDE Drive - Photo 26](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1467861798r.jpg) ![5290 HILLSIDE Drive - Photo 27](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2079291085r.jpg) ![5290 HILLSIDE Drive - Photo 28](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3038305413r.jpg) ![5290 HILLSIDE Drive - Photo 29](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f31222932r.jpg) ![5290 HILLSIDE Drive - Photo 30](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1695527978r.jpg) ![5290 HILLSIDE Drive - Photo 31](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2721977720r.jpg) ![5290 HILLSIDE Drive - Photo 32](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3511304361r.jpg) ![5290 HILLSIDE Drive - Photo 33](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1029198421r.jpg) ![5290 HILLSIDE Drive - Photo 34](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1363863083r.jpg) ![5290 HILLSIDE Drive - Photo 35](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1665372682r.jpg) ![5290 HILLSIDE Drive - Photo 36](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f293384404r.jpg) ![5290 HILLSIDE Drive - Photo 37](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2250035056r.jpg) ![5290 HILLSIDE Drive - Photo 38](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3228741547r.jpg) ![5290 HILLSIDE Drive - Photo 39](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2564642500r.jpg) ![5290 HILLSIDE Drive - Photo 40](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1897304444r.jpg) ![5290 HILLSIDE Drive - Photo 41](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f106757536r.jpg) ![5290 HILLSIDE Drive - Photo 42](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3258532946r.jpg) ![5290 HILLSIDE Drive - Photo 43](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f4185153748r.jpg) ![5290 HILLSIDE Drive - Photo 44](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f819122495r.jpg) ![5290 HILLSIDE Drive - Photo 45](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2068661694r.jpg) ![5290 HILLSIDE Drive - Photo 46](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1401938891r.jpg) ![5290 HILLSIDE Drive - Photo 47](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f14889181r.jpg) ![5290 HILLSIDE Drive - Photo 48](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3632735605r.jpg) ![5290 HILLSIDE Drive - Photo 49](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3105302620r.jpg) ![5290 HILLSIDE Drive - Photo 50](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f4238131110r.jpg) ![5290 HILLSIDE Drive - Photo 51](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1923874850r.jpg) ![5290 HILLSIDE Drive - Photo 52](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f3000845050r.jpg) ![5290 HILLSIDE Drive - Photo 53](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f343520185r.jpg) ![5290 HILLSIDE Drive - Photo 54](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2565419924r.jpg) ![5290 HILLSIDE Drive - Photo 55](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2863856825r.jpg) ![5290 HILLSIDE Drive - Photo 56](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2430632972r.jpg) ![5290 HILLSIDE Drive - Photo 57](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1320114588r.jpg) ![5290 HILLSIDE Drive - Photo 58](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f4007255650r.jpg) ![5290 HILLSIDE Drive - Photo 59](http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f398359406r.jpg) --- **MLS#:** VAFQ2024370 | **Updated:** 2026-10-23 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/5290-hillside-drive-warrenton-va-20187-c3dea66164ad4b7899cbd3d7020e5672) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/5290-hillside-drive-warrenton-va-20187-c3dea66164ad4b7899cbd3d7020e5672#listing", "url": "https://staging.propertysimple.ai/listing/5290-hillside-drive-warrenton-va-20187-c3dea66164ad4b7899cbd3d7020e5672", "name": "5290 HILLSIDE Drive, Warrenton, VA 20187", "description": "AMAZING VALUE! TWO COMPLETE LIVING SPACES - ONE PROPERTY. Rare multigenerational/income producing opportunity on the DC side of Warrenton! A beautifully updated main home PLUS an approximately 1,600-sq.-ft. private apartment with its own kitchen, bedroom, handicap accessible bathroom, entrance, HVAC, water heater and additional basement space. Welcome to this truly one-of-a-kind property offering the perfect blend of flexibility, privacy, and modern updates on 1.5 acres with a flat, usable backyard. With no HOA, you'll have the freedom to bring your chickens, start a garden, park your RV or boat, or simply enjoy the space without restrictive covenants. Whether you're looking for multigenerational living, an income-producing opportunity, or simply extra space for guests, this turnkey home delivers. The standout feature is the approximately 1,600-square-foot private apartment addition, fully remodeled in July 2026, with its own main-level entrance and welcoming front porch, this thoughtfully designed space features freshly refinished hardwood floors, soaring vaulted ceilings, fresh paint, a spacious bedroom overlooking the private backyard, and a beautifully renovated handicap-accessible bathroom. The updated kitchen (July 2026) includes a gas range, dishwasher, and modern finishes. The apartment also includes its own private basement with laundry, a remodeled full bathroom, and a separate exterior entrance. Previously configured with a kitchenette, the existing hookups make it easy to convert the space back into a kitchenette, creating an ideal studio apartment or potential sixth bedroom with its own private living area. A brand-new HVAC system and water heater provide added peace of mind. For maximum flexibility, the apartment also connects to the main home through secure double doors, allowing complete privacy for rental use while maintaining the option to seamlessly incorporate it into the main residence. The main home was extensively remodeled in 2016 and features an impressive gourmet kitchen with a gas cooktop, stainless steel appliances, upgraded cabinetry, and two beautiful 1800s English yellow pine antiques that were thoughtfully repurposed into a stunning 6-foot kitchen island and an undermount double-sink cabinet, all topped with durable, heat-resistant quartz countertops. Rich walnut hardwood flooring flows throughout the main level, where you'll also find a cozy gas fireplace, three spacious bedrooms, and two beautifully updated full bathrooms. The walkout lower level offers even more living space with a large recreation room, a fourth bedroom, and a remodeled full bathroom. Fresh paint and new carpet throughout the home make it completely move-in ready. Major system updates include the roof, windows, HVAC systems, hot water heaters, and deck-all replaced within the past 10 years, making this home as practical as it is beautiful. Step outside to enjoy the oversized deck overlooking a completely private, flat backyard-perfect for entertaining, gardening, or simply relaxing in your own peaceful retreat. Ideally located on the highly desirable DC side of Warrenton, just 1/2 mile from Route 29, this home offers exceptional convenience for commuters, with I-66 and the Gainesville commuter lot just 10 minutes away. Enjoy quick access to shopping and dining at Virginia Gateway, including Wegmans, Target, movie theatre, restaurants, breweries, wineries, golf courses, parks, and the charm of Historic Old Town Warrenton-all while coming home to the peace and privacy of country living.", "image": [ "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f860611200r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1949371680r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2297074354r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2083937616r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f1170384392r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2028378027r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f583654044r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2915503616r.jpg", "http://lh.rdcpix.com/d5bd921273bbc75f7a8c9895a3d3a991l-f2298867509r.jpg", 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